CA2581627A1 - Ph stable chromatographic media using templated multilayer organic/inorganic grafting - Google Patents

Ph stable chromatographic media using templated multilayer organic/inorganic grafting Download PDF

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Publication number
CA2581627A1
CA2581627A1 CA002581627A CA2581627A CA2581627A1 CA 2581627 A1 CA2581627 A1 CA 2581627A1 CA 002581627 A CA002581627 A CA 002581627A CA 2581627 A CA2581627 A CA 2581627A CA 2581627 A1 CA2581627 A1 CA 2581627A1
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CA
Canada
Prior art keywords
chromatographic media
carbon atoms
silica gel
sorbent
moiety containing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002581627A
Other languages
French (fr)
Other versions
CA2581627C (en
Inventor
Ismail M. Rustamov
Michael C. Chitty
Tivadar Farkas
Lawrence Loo
Emmet Welch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Phenomenex Inc
Original Assignee
Phenomenex, Inc.
Ismail M. Rustamov
Michael C. Chitty
Tivadar Farkas
Lawrence Loo
Emmet Welch
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Phenomenex, Inc., Ismail M. Rustamov, Michael C. Chitty, Tivadar Farkas, Lawrence Loo, Emmet Welch filed Critical Phenomenex, Inc.
Publication of CA2581627A1 publication Critical patent/CA2581627A1/en
Application granted granted Critical
Publication of CA2581627C publication Critical patent/CA2581627C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3214—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the method for obtaining this coating or impregnating
    • B01J20/3225—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the method for obtaining this coating or impregnating involving a post-treatment of the coated or impregnated product
    • B01J20/3227—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the method for obtaining this coating or impregnating involving a post-treatment of the coated or impregnated product by end-capping, i.e. with or after the introduction of functional or ligand groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3285—Coating or impregnation layers comprising different type of functional groups or interactions, e.g. different ligands in various parts of the sorbent, mixed mode, dual zone, bimodal, multimodal, ionic or hydrophobic, cationic or anionic, hydrophilic or hydrophobic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3289—Coatings involving more than one layer of same or different nature

Abstract

An advanced silica gel sorbent for use in chromatographic separations that has been chemically modified by surface polycondensation of a trifunctional and/or difunctional organosilane. The chromatographic media exhibits a wider pH range and improved pH stability as compared to other silica gel based sorbents, while retaining all other positive aspects attributed to silica gel based sorbents. A method of forming the advanced silica gel sorbent by Templated Multilayer Inorganic/Organic Grafting.

Claims (13)

1. A chromatographic media comprising a silica gel sorbent, wherein the sorbent has one or more chemical modifiers present on its surface selected from the group consisting of trifunctional and difunctional organosilanes.
2. The chromatographic media of Claim 1, wherein the silica gel sorbent is selected from the group consisting of porous or non-porous silica particles, membranes, monolithic supports, fused capillaries, and silicon or glass wafers having silanols on their surface.
3. The chromatographic media of Claim 1, wherein the organosilanes have the formula R1a R2b SiX4-a-b or R(R1a SiX3-a)n, wherein R is a substituted aliphatic, cyclic, arylic or aromatic organic moiety containing 1 to 8 carbon atoms, R1 and R2 are organic ligands containing 1 to 4 carbon atoms, X is a leaving group attached to the silicon atom, a and b are positive integers equal to 0 or 1, a plus b equals to 1 or 2 but never 0, and n is a positive integer between 2 to 8.
4. The chromatographic media of Claim 3, wherein R is an unsubstituted aliphatic, cyclic, arylic or aromatic organic moiety containing 1 to 8 carbon atoms.
5. The chromatographic media of Claim 4, wherein R is an unsubstituted, saturated aliphatic organic moiety containing 1 to 8 carbon atoms.
6. The chromatographic media of Claim 3, wherein R contains 1 to 3 carbon atoms.
7. The chromatographic media of Claim 3, wherein R1 and R2 contain 1 to 2 carbon atoms.
8. The chromatographic media of Claim 3, wherein X is selected from the group consisting of Cl, OCH3, OC2H5, (CH3)2N, (CH3CH2)2N, I, Br, CN, OOCH3, O(CO)CH3, and O3SCF3.
9. The chromatographic media of Claim 3, wherein n is equal to 2.
10. The chromatographic media of Claim 1 further comprising organosilanes having the formula R1SiX3, R1R2SiX2, or R1R22SiX, wherein R1 and are organic ligands.
11. A method of forming a silica gel sorbent for use in chromatographic separations that has been chemically modified by surface polycondensation of an inorganic/organic modifier comprising the steps:

a. reacting the anhydrous silica gel sorbent with the inorganic/organic modifier, wherein the modifier has the formula R1 a R2b SiX4-a-b or R(R1a S1X3-a)n, wherein R is a substituted aliphatic, cyclic, arylic or aromatic organic moiety containing 1 to 8 carbon atoms or an unsubstituted aliphatic, cyclic, arylic or aromatic organic moiety containing 1 to 8 carbon atoms, R1 and R2 are organic ligands containing 1 to 4 carbon atoms, X is a leaving group attached to the silicon atom, a and b are positive integers equal to 0 or 1, a plus b equals to 1 or 2 but never 0, and n is a positive integer between 2 to 8;
b. hydrolyzing any unreacted leaving groups; and c. dehydrating the sorbent.
12. The method of Claim 11, wherein steps a, b, and c are performed 2 to 15 times.
13. The method of Claim 12, wherein steps a, b, and c are performed 2 to 4 times.
CA2581627A 2004-10-01 2005-09-30 Ph stable chromatographic media using templated multilayer organic/inorganic grafting Active CA2581627C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US61509304P 2004-10-01 2004-10-01
US60/615,093 2004-10-01
US61581204P 2004-10-04 2004-10-04
US60/615,812 2004-10-04
PCT/US2005/035217 WO2006039507A2 (en) 2004-10-01 2005-09-30 Ph stable chromatographic media using templated multilayer organic/inorganic grafting

Publications (2)

Publication Number Publication Date
CA2581627A1 true CA2581627A1 (en) 2006-04-13
CA2581627C CA2581627C (en) 2012-12-11

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Family Applications (1)

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CA2581627A Active CA2581627C (en) 2004-10-01 2005-09-30 Ph stable chromatographic media using templated multilayer organic/inorganic grafting

Country Status (8)

Country Link
US (2) US7563367B2 (en)
EP (1) EP1804950B1 (en)
JP (1) JP5021479B2 (en)
AU (1) AU2005291937A1 (en)
CA (1) CA2581627C (en)
DK (1) DK1804950T3 (en)
ES (1) ES2579756T3 (en)
WO (1) WO2006039507A2 (en)

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Also Published As

Publication number Publication date
US7563367B2 (en) 2009-07-21
ES2579756T3 (en) 2016-08-16
WO2006039507A2 (en) 2006-04-13
EP1804950B1 (en) 2016-06-01
CA2581627C (en) 2012-12-11
US20090275469A1 (en) 2009-11-05
EP1804950A4 (en) 2008-05-07
US8658038B2 (en) 2014-02-25
JP2008514425A (en) 2008-05-08
US20060070937A1 (en) 2006-04-06
JP5021479B2 (en) 2012-09-05
WO2006039507A3 (en) 2006-09-08
AU2005291937A1 (en) 2006-04-13
EP1804950A2 (en) 2007-07-11
DK1804950T3 (en) 2016-06-20

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